Issue 16, 2000

NMR studies of tautomerism in the fungal melanin biosynthesis intermediate 1,3,8-trihydroxynaphthalene

Abstract

The naphthol reductase catalysed conversion of 1,3,8-trihydroxynaphthalene (T3HN) to vermelone has been studied using a partially purified cell-free enzyme preparation from Verticillium dahliae. NMR studies show that in aqueous buffer T3HN exists as an equilibrium mixture of the parent phenol and a keto-tautomer. 1,3,6,8-Tetrahydroxynaphthalene (T4HN) is a more efficient substrate than T3HN for the naphthol reductase. 1,3-Dihydroxynaphthalene also acts as a substrate and is converted to 8-deoxyvermelone.

Article information

Article type
Paper
Submitted
13 Mar 2000
Accepted
15 Jun 2000
First published
19 Jul 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2771-2775

NMR studies of tautomerism in the fungal melanin biosynthesis intermediate 1,3,8-trihydroxynaphthalene

T. J. Simpson and M. K. Bandumathie Weerasooriya, J. Chem. Soc., Perkin Trans. 1, 2000, 2771 DOI: 10.1039/B002030N

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